Operations Lead

About this role

ABOUT CROSBY

Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.

Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.

Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.

Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first X employees at Ramp). We work together, in person, in New York City — because the best ideas still happen in the same room. Help us transform one of society's most important industries.

Welcome to Crosby, the next generation law company!

We're a team of technologists and legal experts collaborating closely to reimagine corporate legal services from the ground up. We build proprietary technology and human in the loop workflows to radically enhance the lawyer machine relationship. Our mission is to review complex documents faster than ever and with perfect quality

Crosby was founded by Ryan (Penn, Stanford Law, ex Cooley, former GC) and John (Penn M&T, ex Ramp, ex Google)

We believe:

- A great legal system is the watermark of a great society.

- Legal work is art and science. We are discovering the frontier between the two— codifying what can be systematized, and amplifying human expertise where judgment matters most.

- The right way to deploy AI in law isn’t by selling software. It’s by selling outcomes — higher-quality legal work, delivered faster and more efficiently

- In an in-person culture at our NYC office.

WE BELIEVE:

- A great legal system is the watermark of a great society.

- Legal work is an art and science. We want to discover the frontier between the two and codify the scientific parts, which is a magnificent puzzle.

- Selling work, not software, is the best way to realize the productivity gains of GenAI for professional services.

- In an in-person culture at our NYC office.

THE ROLE:

This is not your typical bizops role. Operations are core to our business and are a competitive advantage, so we are designing an ambitious, world class org.

As a member of the Operations Team at Crosby, you will take full ownership of scaling the best law firm ever built – designing and optimizing complex human-in-the-loop workflows, cracking our automation, and ensuring quality.

WHAT YOU’LL DO:

- Own mission-critical workflows that blend human and machine to deliver legal work faster and better than ever before

- Design and implement new operational processes, from scoping to rollout, across legal delivery, quality control, training, and client success.

- Partner with product and engineering to prototype and deploy internal tools that increase throughput and reduce error.

- Define and operationalize Crosby’s evolving playbooks, training systems, and incentives as we scale.

WHAT WE’RE LOOKING FOR:

- 2–5 years of experience in operations, consulting, finance, or a similarly analytical and high pressure, execution-focused environment. Priority given to former founders.

- Deep curiosity about how things work—and how they can work better.

- Proven ability to own complex systems or projects end-to-end, especially in ambiguous or high-stakes settings.

- Excitement about working in-person with a team that values precision, pace, and constant reinvention.

- An interest in law or legal services is a plus, but not required—this is an operations-first role.

WHY WORK AT CROSBY LEGAL:

- Competitive salary and equity compensation.

- Comprehensive health, dental, and vision insurance.

- Unlimited PTO

- In-person team in NYC with a collaborative, high-energy environment.

Apply now to join Crosby and be part of transforming the legal landscape.

Note: Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. Pursuant to New York Labor Law Section 194-b, US Pay Range is $140,000 - $185,000 which represents the base salary we reasonably expect to pay for this position at the time of this posting. Final compensation will be determined based on skills, experience, and qualifications.

EQUAL OPPORTUNITY

Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.

Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.

Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.

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